Triethylamine → Tert-butyl 4-(2,5-dicyano-3,4,6-trifluorophenyl)piperazine-1-carboxylate

HRID 595015

Reaktionsgleichung

Reaktionsgleichung von HRID 595015
F[C:2]1[C:9]([F:10])=[C:8]([C:11]#[N:12])[C:7]([F:13])=[C:6]([F:14])[C:3]=1[C:4]#[N:5].[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C>CC(C)=O.O>[C:4]([C:3]1[C:6]([F:14])=[C:7]([F:13])[C:8]([C:11]#[N:12])=[C:9]([F:10])[C:2]=1[N:18]1[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]1)#[N:5]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 15783TetrafluoroterephthalonitrileHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 86671743Tert-butyl 4-(2,5-dicyano-3,4,6-trifluorophenyl)piperazine-1-carboxylateAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

2,3,5,6-tetrafluoroterephthalonitrile (1 g, 5 mmol) was dissolved in acetone (15 mL) in a 2-necked flask under Nitrogen. A solution of tert-butyl piperazine-1-carboxylate (1.39 g, 7.5 mmol) in water (3 mL) was then added followed by triethylamine (1.01 g, 10 mmol). The solution was heated to 55° C. for 8 h then cooled to rt. The resulting solid was filtered then washed with acetone. The filtrate was concentrated under vacuum and the residue was dissolved again in DCM (30 mL) and washed once with 1M HCl (30 mL) and once with brine (30 mL). The organics were dried over Na2SO4, filtered and the solvent removed in vacuo to give tert-butyl 4-(2,5-dicyano-3,4,6-trifluorophenyl)piperazine-1-carboxylate as a bright yellow solid (0.938 g, 51% yield).

Aufarbeitung

  1. temperaturethen cooled to rt
  2. filtrationThe resulting solid was filtered
  3. washthen washed with acetone
  4. concentrationThe filtrate was concentrated under vacuum
  5. dissolutionthe residue was dissolved again in DCM (30 mL)
  6. washwashed once with 1M HCl (30 mL) and once with brine (30 mL)
  7. dry with materialThe organics were dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a1c2be596b64a1daf884580694e7663
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242987B2

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